On the Supreme Court, Brennan was known for his outspoken progressive views, including opposition to the death penalty and support for abortion rights. He authored several landmark case opinions, including Baker v. Carr, establishing the "one person, one vote" principle, and New York Times Co. v. Sullivan, which required "actual malice" in a libel suit against public officials. Due to his ability to shape a wide variety of opinions and "bargain" for votes in many cases, he was considered to be among the Court's most influential members. Justice Antonin Scalia called Brennan "probably the most influential Justice of the [20th] century."[4]

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Brennan was born in Newark, New Jersey, the second of eight children. His parents, William and Agnes (McDermott) Brennan, were Irish immigrants. They met in the United States, although both were originally from County Roscommon in Ireland. His father had little education; he worked as a metal polisher. However, he rose to a position of leadership, serving as the Commissioner of Public Safety for the city of Newark from 1927 to 1930.

Brennan gained the attention of Herbert Brownell, United States Attorney General and Eisenhower's chief legal affairs adviser, when Brennan had to give a speech at a conference (as a substitute for New Jersey Supreme Court Chief Justice Vanderbilt).[11] To Brownell, Brennan's speech seemed to suggest a marked conservatism, especially on criminal matters.[11]

His nomination faced a small amount of controversy from two angles. The National Liberal League opposed the nomination of a Catholic, thinking he would rely on his religious beliefs rather than the Constitution when ruling,[10] and Senator Joseph McCarthy had read transcripts of Brennan's speech where he decried overzealous anti-Communist investigations as "witch-hunts." After a confirmation hearing in 1957 in which Brennan defended himself against McCarthy's attacks and proclaimed that he would rule solely on the basis of the Constitution and not on Church law,[12] he was confirmed by a near-unanimous vote, with only Senator McCarthy voting against him.[13]

Other factors playing into Brennan's appointment were his status as a state court judge – no state judge had been appointed to the High Court since Benjamin N. Cardozo in 1932 – and Eisenhower's desire to appear bipartisan after his appointments of two Republicans: Earl Warren (former Governor of California) and John Marshall Harlan II.[14]

An outspoken liberal throughout his career, he played a leading role in the Warren Court's expansion of individual rights. Brennan played a behind-the-scenes role during the Warren Court, coaxing more conservative colleagues to join the Court's decisions. Brennan's opinions with respect to voting (Baker v. Carr), criminal proceedings (Malloy v. Hogan), the free speech and establishment clauses of the First Amendment (Roth v. United States), and civil rights (Green v. County School Board of New Kent County) were some of the most important opinions of the Warren Era. Brennan's role in expanding free speech rights under the First Amendment is particularly notable, as he wrote the Court's opinion in 1964's New York Times Co. v. Sullivan, which created constitutional restrictions on the law of libel. It was Brennan who coined the phrase "chilling effect", in 1965's Dombrowski v. Pfister. His close friendship with Chief Justice Warren, who frequently assigned Brennan the task of writing the majority opinion, led to the other justices nicknaming him the "deputy Chief".

On the more conservative Burger Court, Brennan was a staunch opponent of the death penalty and a supporter of abortion rights, and joined the majority in landmark rulings on both issues (1972's Furman v. Georgia on the death penalty and 1973's Roe v. Wade on abortion). With the ascension of the most conservative member of the court, William Rehnquist, to the position of Chief Justice, and the replacement of Warren Burger and the moderate Lewis Powell with Antonin Scalia and Anthony Kennedy, Brennan found himself more frequently isolated. At times his opinions would be joined only by Thurgood Marshall, as by 1975 the two were the last remaining surviving liberals of the Warren Court (Byron White was the third survivor of the Warren Court during Rehnquist's tenure, but often sided with the conservatives, especially on cases involving criminals or abortion). This likemindedness led to both Brennan and Marshall's clerks referring to them as 'Justice Brennan-Marshall' in the face of the court's heavy conservative opposition to the two. Brennan declared in Furman that he believed the death penalty violated the Eighth Amendment's prohibition on "cruel and unusual" punishment, and for his remaining years on the bench he and Marshall dissented from every case upholding the imposition of the death penalty. He was able to convince no other justice of this view, though Justice Harry Blackmun would eventually agree in 1994, after Brennan's retirement.

In his penultimate and final terms on the Court, he wrote the controversial rulings for Texas v. Johnson and United States v. Eichman, respectively. In both cases, the Court held that the First Amendment protects desecration of the United States flag.

Brennan's wife Marjorie died in 1982. A few months later, in 1983 when he was 77 years old, he married Mary Fowler, who had served as his secretary for 26 years. Brennan's colleagues learned of his second marriage via a short office memo stating, "Mary Fowler and I were married yesterday and we have gone to Bermuda."

Brennan strongly believed in the Bill of Rights, arguing early on in his career that it should be applied to the states in addition to the federal government.[24] He often took positions in favor of individual rights against the state, often favoring criminal defendants, minorities, the poor, and other underrepresented groups. Furthermore, he generally shied away from the absolutist positions of Justices Hugo Black and William O. Douglas, being very amenable to compromise. He was willing to compromise to win a majority of Justices.[25] Brennan's conservative detractors charged that he was a purveyor of judicial activism, accusing him of deciding outcomes before coming up with a legal rationale for them.[26] At his retirement, Brennan said the case he thought was most important was Goldberg v. Kelly, which ruled that a local, state or federal government could not terminate welfare payments to a person without a prior individual evidentiary hearing.[27]

In the 1980s, as the Reagan administration and the Rehnquist Court threatened to "roll back" the decisions of the Warren Court, Brennan became more vocal about his jurisprudential views. In a 1985 speech at Georgetown University, Brennan criticized Attorney General Edwin Meese's call for a "jurisprudence of original intention" as "arrogance cloaked as humility"[28] and advocated reading the U.S. Constitution to protect rights of "human dignity."

Brennan was also less interested in stare decisis or the avoidance of "absolutist" positions where the death penalty was concerned. Brennan and Thurgood Marshall, Brennan's closest ally in the court, concluded in Furman v. Georgia that the death penalty was, in all circumstances, unconstitutional, and never accepted the legitimacy of Gregg v. Georgia, which ruled that the death penalty was constitutional four years later. Thereafter, Brennan or Marshall took turns, joined by the other, in issuing a dissent in every denial of certiorari in a capital case, and from every decision in a case which the court did take which failed to vacate a sentence of death.[29]

Brennan also authored a dissent from the denial of certiorari in Glass v. Louisiana. In Glass, the Court chose not to hear a case that challenged the constitutionality of the use of the electric chair as a form of execution. Brennan wrote:[30]

Th[e] evidence suggests that death by electrical current is extremely violent and inflicts pain and indignities far beyond the "mere extinguishment of life." Witnesses routinely report that, when the switch is thrown, the condemned prisoner "cringes," "leaps," and "fights the straps with amazing strength." "The hands turn red, then white, and the cords of the neck stand out like steel bands." The prisoner's limbs, fingers, toes, and face are severely contorted. The force of the electrical current is so powerful that the prisoner's eyeballs sometimes pop out and "rest on [his] cheeks." The prisoner often defecates, urinates, and vomits blood and drool.

Brennan concluded by stating that electrocution is "nothing less than the contemporary technological equivalent of burning people at the stake."

"We current Justices read the Constitution in the only way that we can: as twentieth century Americans. We look to the history of the time of framing and to the intervening history of interpretation. But the ultimate question must be, what do the words of the text mean in our time. For the genius of the Constitution rests not in any static meaning it might have had in a world that is dead and gone, but in the adaptability of its great principles to cope with current problems and current needs."[31]

"The nations of the world, faced with sudden threats to their own security, will look to Israel's experience in handling its continuing security crisis, and may well find in that experience the expertise to reject the security claims that Israel has exposed as baseless and the courage to preserve the civil liberties that Israel has preserved without detriment to its security."[32]

"Successive generations of Americans have continued to respect these fundamental choices and adopt them as their own guide to evaluating quite different historical practices. Each generation has the choice to overrule or add to the fundamental principles enunciated by the Framers; the Constitution can be amended or it can be ignored."[31]

"The constitutional vision of human dignity rejects the possibility of political orthodoxy imposed from above; it respects the right of each individual to form and to express political judgments, however far they may deviate from the mainstream and however unsettling they might be to the powerful or the elite." "[31]

"The dissemination of ideas can accomplish nothing if otherwise willing addressees are not free to receive and consider them. It would be a barren marketplace of ideas that had only sellers and no buyers." Lamont v. Postmaster General, 381 U.S. 301 (1965) (concurring).

"Sex, a great and mysterious motive force in human life, has indisputably been a subject of absorbing interest to mankind through the ages." Roth v. United States, 354 U.S. 476 (1957).

"[W]e consider this case against the background of a profound national commitment to the principle that debate on public issues should be uninhibited, robust, and wide-open, and that it may well include vehement, caustic, and sometimes unpleasantly sharp attacks on government and public officials." New York Times Co. v. Sullivan, 376 U.S. 254 (1964).

"I cannot accept the notion that lawyers are one of the punishments a person receives merely for being accused of a crime." Jones v. Barnes, 463 U.S. 745, 764 (1983) (dissenting).

"Those whom we would banish from society or from the human community itself often speak in too faint a voice to be heard above society's demand for punishment. It is the particular role of courts to hear these voices, for the Constitution declares that the majoritarian chorus may not alone dictate the conditions of social life." McCleskey v. Kemp, 481 U.S. 279 (1987) (dissenting).

"The Court next states that its unwillingness to regard petitioner's evidence as sufficient is based in part on the fear that recognition of McCleskey's claim would open the door to widespread challenges to all aspects of criminal sentencing...Taken on its face, such a statement seems to suggest a fear of too much justice." McCleskey v. Kemp", 481 U.S. 279 (1987) (dissenting).

"If the Court had struck down legislative prayer today, it would likely have stimulated a furious reaction. But it would also, I am convinced, have invigorated both the 'spirit of religion' and the 'spirit of freedom.'" Marsh v. Chambers, 463 U.S. 783 (1983) (dissenting).

"If the right of privacy means anything, it is the right of the individual, married or single, to be free from unwarranted governmental intrusion into matters so fundamentally affecting a person as the decision whether to bear or beget a child." Eisenstadt v. Baird, 405 U.S. 438 (1972).

"We can imagine no more appropriate response to burning a flag than waving one's own, no better way to counter a flag burner's message than by saluting the flag that burns, no surer means of preserving the dignity even of the flag that burned than by – as one witness here did – according its remains a respectful burial. We do not consecrate the flag by punishing its desecration, for in doing so we dilute the freedom that this cherished emblem represents." Texas v. Johnson, 491 U.S. 397 (1989).

^Robotti, Michael P. (2009). "Separation of Powers and the Exercise of Concurrent Constitutional Authority in the Bivens Context". Connecticut Public Interest Law Journal. 8: 171.

^Daniel, Scott R. (2008). "The Spy Who Sued the King: Scaling the Fortress of Executive Immunity for Constitutional Torts in Wilson v. Libby". American University Journal of Gender, Social Policy & the Law. 16: 503.